Middlebrook Vacation Rentals

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Our top choices for Middlebrook vacation rentals

Beautiful 3-bedroom house with AC in charming Middlebrook

Beautiful 3-bedroom house with AC in charming Middlebrook
Middlebrook
The price is CA $266
CA $464 total
includes taxes & fees
May 17 - May 18
Beautiful 3-bedroom house with AC in charming Middlebrook

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (55 reviews)
"Friendly staff "
United States
Kyle
The price is CA $108
CA $120 total
includes taxes & fees
May 17 - May 18
Affordable Suites of America Waynesboro

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (231 reviews)
"Clean and had a kitchenette area with stove, fridge. Felt very safe."
United States
Kurt
The price is CA $143
CA $160 total
includes taxes & fees
May 13 - May 14
Valley Extended Suites

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Roseland
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
The price is CA $164
CA $339 total
includes taxes & fees
May 31 - Jun 1
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front

The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front
Buena Vista
9.8 out of 10, Exceptional, (27 reviews)
"Nice and cozy home for overnight stays "
United States
Yahima O.
The price is CA $137
CA $259 total
includes taxes & fees
May 10 - May 11
The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front

NEW! Cheerful 2 bd bungalow with hot tub. Must see!

NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Waynesboro
9.8 out of 10, Exceptional, (55 reviews)
"Our host did a great job!! She thought of everything to make your stay enjoyable. We will definitely be returning."
United States
Cora S.
The price is CA $160
CA $280 total
includes taxes & fees
May 21 - May 22
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Wintergreen Resort
10.0 out of 10, Exceptional, (35 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
The price is CA $157
CA $445 total
includes taxes & fees
May 31 - Jun 1
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (16 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is CA $194
CA $300 total
includes taxes & fees
Jun 8 - Jun 9
Love Ridge Mountain Lodging

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (60 reviews)
"The room was very clean and conveniently located for us."
United States
Jeanell S.
The price is CA $113
CA $156 total
includes taxes & fees
May 10 - May 11
The Firefly Springhouse

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (110 reviews)
"Great and comfortable place to stay! Host was very welcoming and responsive. "
United States
Jon L.
The price is CA $228
CA $449 total
includes taxes & fees
May 11 - May 12
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (103 reviews)
"The mountain views from the balcony are spectacular!"
United States
Becca R.
The price is CA $112
CA $334 total
includes taxes & fees
May 11 - May 12
Endless Mountain Top Views from All The Way Up!

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Roseland
10.0 out of 10, Exceptional, (102 reviews)
"This place is such a gem. Stunning property, clean, and comfortable. You can tell the hosts take a lot of pride in this place. Loved it. "
United States
Warren
The price is CA $178
CA $270 total
includes taxes & fees
May 10 - May 11
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (56 reviews)
"The place was very clean and spacious. The communication from the hosts was helpful. We had a very pleasant stay."
United States
James S.
Spacious + Serene Mtn Top Escape, 4 En Suites

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (152 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is CA $150
CA $336 total
includes taxes & fees
May 31 - Jun 1
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Waynesboro
10.0 out of 10, Exceptional, (20 reviews)
"The perfect stay for a wedding weekend in Waynesboro. It was very warm and accommodating and I can’t say enough good things about it. Thank you for a great weekend"
United States
Michael W.
The price is CA $154
CA $255 total
includes taxes & fees
May 10 - May 11
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (34 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
The price is CA $156
CA $366 total
includes taxes & fees
May 10 - May 11
Wintergreen Condo -Steps to Ski and restaurants

Autumn Ridge Cottages

Autumn Ridge Cottages
2.5 star property
Lexington
9.0 out of 10, Wonderful, (180 reviews)
"Very nicely appointed, clean, quiet, quaint, and close to family. "
United States
Gary
The price is CA $376
CA $591 total
includes taxes & fees
May 11 - May 12
Autumn Ridge Cottages

High Meadows--King BR, fireplace, jacuzzi, kitchen

High Meadows--King BR, fireplace, jacuzzi, kitchen
Lyndhurst
9.8 out of 10, Exceptional, (16 reviews)
"Nice quiet and clean. Fireplace was excellent. "
United States
april h.
The price is CA $294
CA $376 total
includes taxes & fees
May 11 - May 12
High Meadows--King BR, fireplace, jacuzzi, kitchen

Whimsical Creekside Cabin

Whimsical Creekside Cabin
Vesuvius
10.0 out of 10, Exceptional, (56 reviews)
"The place & everything was great!"
United States
Major G.
The price is CA $135
CA $303 total
includes taxes & fees
May 12 - May 13
Whimsical Creekside Cabin

Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (127 reviews)
"great stay"
United States
Vickie G.
The price is CA $159
CA $352 total
includes taxes & fees
May 17 - May 18
Escape to the Blue Ridge Mountains at Wine-tergreen!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middlebrook Hotel Reviews

Find out more about Middlebrook

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middlebrook. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Middlebrook?

Yes, we offer vacation rentals near top attractions in Middlebrook, or you can select a more secluded option if you'd like a relaxing place to stay. Middlebrook is known for its parks.

What are some of the best vacation rentals in Middlebrook?

Alone Mill Schoolhouse - A paradise for outdoor lovers: This vacation home rental outside of Middlebrook is located on the waterfront and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

What can I see and do in Middlebrook?

While exploring the area, visit family-friendly sights like Beverley Cigar Store, or get outside and enjoy nature at George Washington National Forest. In the larger area, you’ll find Staunton Railroad Station and Frontier Culture Museum.

What are vacation rentals like in Middlebrook?

Vacation rentals are private accommodations you can reserve for a couple days or more in Middlebrook. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip.